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Not even the leader of the free world is boss enough to mix it up with angry Boston fans.

Everyone knows that President Barack Obama is a huge sports guy. He’s hosted pickup games with NBA stars. He’s made his allegiance to all things Chicago-teams related no secret. Heck, he’s even appeared on Bill Simmons’ B.S. podcast. So, given all that, his sports knowledge is clearly beyond reproach.

His judgment, though? Eh…

During a recent appearance in Boston, President Obama made the gaffe of all gaffes, the mistake of all mistakes – he didn’t properly gauge his audience.

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A mere day after beloved Red Sox workhorse, Kevin Youkilis, was shipped off to the Chicago White Sox for the baseball equivalent of pennies, the POTUS taunted Red Sox fans a bit.

Naturally, it didn’t go well. Check it out:

The lesson here? Boston fans will boo anyone, even if it’s the Commander in Chief, who takes a shot -- no matter how slight -- at their beloved sports teams.